7-Amino-3-azidomethyl-3-cephem-4-carboxylic acid → 7-[3-Methyl-1,2,4-oxadiazol-5-yl-acetamido]-3-azidomethyl-3-cephem-4-carboxylic acid

HRID 971711Notes

Reaction equation

HRID 971711 reaction equation
[CH3:1][C:2]1[N:6]=[C:5]([CH2:7][C:8]([OH:10])=O)[O:4][N:3]=1.[NH2:11][CH:12]1[C:26](=[O:27])[N:14]2[C:15]([C:23]([OH:25])=[O:24])=[C:16]([CH2:19][N:20]=[N+:21]=[N-:22])[CH2:17][S:18][C@H:13]12>C(#N)C>[CH3:1][C:2]1[N:6]=[C:5]([CH2:7][C:8]([NH:11][CH:12]2[C:26](=[O:27])[N:14]3[C:15]([C:23]([OH:25])=[O:24])=[C:16]([CH2:19][N:20]=[N+:21]=[N-:22])[CH2:17][S:18][C@H:13]23)=[O:10])[O:4][N:3]=1

Participants

4

Reactant 2

HCID 128022197-Amino-3-azidomethyl-3-cephem-4-carboxylic acidHCID 213130182-(3-Methyl-1,2,4-oxadiazol-5-yl)acetic acid

Product 1

HCID 1317115777-[3-Methyl-1,2,4-oxadiazol-5-yl-acetamido]-3-azidomethyl-3-cephem-4-carboxylic acidYield 35%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Using the same procedure, 5.51 mmol of 3-methyl-1,2,4-oxadiazol-5-yl-acetic acid and 5.51 mmol of 7-amino-3-azidomethyl-3-cephem-4-carboxylic acid (90% purity) in 55 ml of dry acetonitrile were reacted for one hour at room temperature and 11/2 hours at 50° C. to obtain a 35% yield of pure 7-[3-methyl-1,2,4-oxadiazol-5-yl-acetamido]-3-azidomethyl-3-cephem-4-carboxylic acid with a recovery of 45% of 7-amino-3-azidomethyl-cephalosporanic acid.

Workup

  1. customwere reacted for one hour at room temperature

Sources & evidence

ORD record
ord-44c7769bfb194dbfa7d430012101eda3
Source dataset
uspto-grants-1979_07
Patent number
US04160829

Reaction notes

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